4-Chlorophenol → HCID 53948317, compound

HRID 1462655Notes

Reaction equation

HRID 1462655 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C[O-].[Na+].[Cl:12][C:13](Cl)=[CH:14][C:15]([CH3:19])([CH3:18])[CH:16]=[CH2:17]>CN(C)C=O>[Cl:12][CH:13]=[C:14]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:15]([CH3:19])([CH3:18])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 10942334Sodium MethoxideHCID 13089648HCID 13089648, compound

Product 1

HCID 53948317HCID 53948317, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

51.4 g (0.4 mol) of p-chlorophenol are reacted, in 300 ml of dimethylformamide, with 80 ml of 30% strength sodium methylate solution (0.4 mol), and the solvent is then stripped off at 30 mbar. 33 g (0.2 mol) of 1,1-dichloro-3,3-dimethyl-1,4-pentadiene are then added to the mixture, and the latter is heated under reflux during the course of 9 hours. The working-up is according to Example A1(a). The distillation at a boiling point of 122°-130° C./0.2 mm Hg yields 44.8 g of 1-chloro-3,3-dimethyl-2-(p-chlorophenoxy)-1,4-pentadiene, which are 87% of theory.

Workup

  1. temperaturethe latter is heated
  2. temperatureunder reflux during the course of 9 hours
  3. distillationThe distillation at a boiling point of 122°-130° C./0.2 mm Hg

Sources & evidence

ORD record
ord-e3a7b88dd4414afcbd03363551b50bbe
Source dataset
uspto-grants-1984_07
Patent number
US04460793

Reaction notes

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